If you have a thing about cartography, Reddit’s “MapPorn” page is almost too much to bear. If you also have a thing about travel as well, beware – this one can devour entire afternoons. For example, here’s one map that has captured the imaginations of thousands of globetrotting enthusiasts in a way its creator never intended.

What’s the shortest route that will take you through every country in the world? Reddit user e8odie, laid up in bed with a broken leg, decided to find out. When he posted the resulting map on the site, the comments went nuts. Why? Because even though the map was clearly labelled a thought-experiment, most of the fun was imagining if it was a real land route. Just how practical is it? The general consensus: “not very.”

Here are a few obstacles we spotted for this ultimate round-the-world trip.1. Darien Gap
The route takes you from Panama to Colombia by plunging into the Darien Gap, a sprawling mat of swampland and forest that was described by the journalist Robert Young Pelton as “probably the most dangerous place in the Western Hemisphere”. Expect such life-affirming delights as virtually impassable jungle, drug traffickers, kidnappers, understandably trigger-happy paramilitary troops and a truly profound lack of good roads. It’s perfectly possible to visit the Darien Gap, but crossing it? Have fun.

2. Russia By Land
Putting aside the bureaucratic nightmare of getting permission to cross the Bering Strait on foot (or the hot water you can land in if you don’t get it), there’s the small matter of crossing a colossal administrative region of Russia called Chukotka Autonomous Okrug. Driving a vehicle designed for even the toughest roads? Too bad, because there aren’t any — barring those laid down in winter. It’s thousands of miles of roadless tundra, forest and Arctic desert. It’s what planes were invented for.

3. North Korea to South Korea
A few years back, it was still possibly to cross the border between Russia and North Korea via the train station at Tumangan — as long as you have the correct visas and a state-approved tour guide. It may still be possible, although it’s certainly not part of North Korea’s attempt to build a tourism industry. You might make it all the way down to the DMZ — but from there? Forget it. Retrace your steps and take the ferry.

4. Israel to Lebanon
Welcome to the Rosh HaNikra border crossing, administered by the United Nations and the Israel Defense Forces. Are you a diplomat or UN official? Do you work well in conditions of extreme diplomatic tension? Can you run faster than Usain Bolt? If your answers to all of these questions aren’t “yes,” stay clear.

5. Armenia to Azerbaijan
Staying with the happy topic of violent border clashes, let’s consider Armenia and Azerbaijan. They went to war in the early ’90s — a situation that endured as a mutually hostile standoff. This “frozen conflict” thawed in 2011 and it’s still pumping out a fair bit of heat. Right now, that border is officially closed — and trying to enter Azerbaijan with a passport that shows signs of being used in Armenia is a fairly terrible idea.

I shrug off my rucksack, collapse onto the bed and wait to arrive. At some point I doze off.

When I awake, it’s late afternoon. Toronto is hot – freakishly so, my host later tells me – and when I step outside, I have to learn to breathe again. My frail English constitution is confused – should I start sweating, or just save time by dying on the spot? I wander through the baking heat in search of a Starbucks. This is my first time in Canada – or it will be, when I finally get here.

I hate flying for so many reasons. If you want to break the ice with the average Brit, ask them for their views on membership of the European Union and prepare to have your ears blown off. I’m like that with flying. I used to have a paralyzing fear of takeoff – these days, it has receded to a level of terror I can medicate myself through. But beyond the bottomless abyss of dread that flying hurls me into, I have philosophical issues with it as well. Flying is a technological marvel, and the modern world couldn’t run without it – but it also feels … wrong.

Let’s talk about Morocco for a second. I’ve never been, and I have a romantic fantasy about arriving there for the first time. I’ll be on a ferry, it’ll be dawn and the dim, rose-fingered line of the horizon ahead will be broken, raggedly shadowed as the light gets stronger. Land ho! Over the next hour, Africa will emerge, unveiled and climbing into the light. By the time we dock at Tangiers, I’ll have been staring at African mountains for hours. My brain – always sleep-deprived when I travel, always overloaded with sights and sounds, and probably jittery from too much coffee – will have grown accustomed to the simply insane notion that I’m approaching another continent. This thought process (“Seriously?” “Yes – look.“) would have had time to sink deep enough to change my mind, allowing my thoughts to catch up with reality.

My first impression of Toronto, after being magically shot across the Atlantic in a colossal tube of metal called a 787 is that Peter Jackson’s “The Hobbit” is a lot better than I’d been told. As I stagger into a taxi, I’m still remembering staring fixedly at dwarves on the inflight entertainment screen in an attempt to blot out air turbulence. I’m still doing it as the taxi leaves Pearson Airport and the driver, hearing I write about travel, starts selling Toronto to me. His conversation and my thoughts get mixed: Bilbo Baggins suddenly lives in a condo; Saruman lives up the CN Tower. Upon reaching the door to my apartment, I realize I haven’t eaten for hours and get lost in the memory of chasing a tiny microwaved sausage around my airline meal plate – until I come to, standing there motionless with the key in the door. My thoughts are mired in another time zone. I get indoors and lie on the bed, and nothing feels real.

Imagine how Nilson Tuwe Huni Kui must have felt. He’s the son of the chief of the Huni Kiu Kaxinawa tribes in Brazil, and in March of this year he traveled from an Amazonian village of 600 people to the concrete jungle of New York, to promote his people’s interests and study documentary film-making. His first challenge? Arriving.

“First you arrive physically. But only after a while, your soul gets here too.”

Is it as simple as culture shock? Perhaps for Nilson Tuwe Huni Kui that might be true – but not for me, surely. Canada isn’t so different to the UK. Barring the scale of the architecture and the blue sky overhead, differences seem superficial. I’m charmed by the way police cars look like the ones in “Due South.” I spot a building I’m certain was in “Battlestar Galactica.” But squint and this could be an English city (perhaps one preparing for a bid to be a City of Culture, because everything here is curiously litter-free). This isn’t culture shock, and I’m not Crocodile Dundee.

Then, the most confusing feeling of all – guilt. As if I’m here under false pretenses. In some pseudo-puritanical sense, I feel like I haven’t earned this. I’ve skipped straight to dessert without eating my greens. I’ve cheated. This is of course ludicrous. Should I have tried to cross the Atlantic in a canoe, perhaps, or maybe on a pedalo? Should I swim it with Ben Fogle? It’s absurd – but the feeling lingers, and I think I know the root of it. If I fly somewhere, I’ve missed all the fun of getting there. I’ve cheated myself out of that adventure. However impractical the alternatives, planes are just too fast for my sense of what constitutes “travel.” It seems I’m one of those Slow Movement people, which must explain why I’m so unfit these days.

I doze, wake up, step out into the stifling heat, grab a coffee to go and head towards Downtown. It’s a good hour before the single-story shops of Yonge Street have grown into skyscrapers around me, and that process is gradual, less observed than felt. There no sense of cheating here, no desirable experience dodged. I’m moving at the right speed to arrive, and I do so comfortably. It’s an odd feeling, because here I am, fully present in the middle of Toronto, but still feeling like I haven’t arrived in Canada yet.

It’s only a few days later, staring out of a high-rise window at storm clouds rolling over the city, that I feel a sense of arrival thump within me. My first thought is Ahuh, so they have crappy weather here too – and my second is Ahuh – “here too.” My inner time zones synchronize, and all thoughts of hobbits and sausages leave my mind. I’m finally here, and it’s time to go exploring.

When she was 16, Londoner Jennifer Olive went on holiday with her parents to the British seaside resort of Blackpool. The weather was lousy, their hotel was bland and she can’t remember where they went or what they did. A disappointment? Not so.

“A year later I went backpacking round India, walking one of the spice trails near Kerala. When you got up in the morning you had no idea what would happen that day, or what was ’round the next corner. Plans fell apart; we had to take detours and at one point we got lost and ended up staying with some total strangers. There was this constant sense that anything was possible. I hated it. The following year I went back to Blackpool and I’ve been every year since.”

Like many Britons, Olive believes that good travel is about exploring your comfort zone. A 2012 survey by Rough Guides found that more than three-quarters of Brits have been to the same destination more than once, and one in ten have returned to the same destination more than 10 times. The chief reason? The satisfaction of familiarity. Olive believes this kind of travel meets a basic human need to put down roots wherever you go, making a travel destination feel like a second home.

“It’s obviously important to see the world – but life is just too short to have a string of experiences that fail to meet your expectations. In the 32 years I’ve been spending my summers at Blackpool, I’ve got to know the place in a really deep and lasting way. I know every rundown cafe; I see the same people getting older – it feels familiar in a way India never did. I’ve rented out the same cottage for the last two decades, and at the end of every stay I carve a notch in the wainscoting. There’s a little line of notches there now. It helps me keep track of where the years went.”

Now she’s putting that guiding ethos to work with a startup she hopes will revolutionize 21st century travel. Set to launch in early 2014, Unadventure.com is a luxury tour operator that seeks to present its clients with the ultimate tailored travel experience – down to the very last detail. New customers fill out a 60-page application form and attend a series of interviews in order to build a detailed personality profile, and it’s this profile that determines the kind of holiday they’ll be given. Fond of the British cooked breakfast? That’s how you’ll start your days on your Unadventure holiday. No second language? Unadventure will find the perfect English expat enclave for you, or even ensure you don’t have to leave the country at all. From your favorite reading material to a sightseeing itinerary that guarantees no surprises, the aim is a bespoken holiday that will make you feel you’ve barely left home.

“They say that adventures happen when plans fall apart, and that’s exactly what we’ll seek to avoid at Unadventure.com. Tourism statistics show that most people don’t want to be overwhelmed by their travel experiences – and obviously they don’t want to be underwhelmed. What they want is to be whelmed. We’re going to whelm our customers. As part of the concept trial I anonymously put myself through the profiling process, and at the end, my team built the perfect holiday for me … in Blackpool. I feel that says a lot about the service we’re offering.”

It’s only when you’re walking down the airport runway that you realize how big it really is. Runways are designed on an inhuman scale. If you’re an aircraft, they’re just long enough to claw yourself into the air. This one, Tempelhof runway 9L/27R, is 2,094 meters long. It takes you 20 minutes of brisk walking to cover the distance a Pan Am Boeing 747 would accelerate through in 60 seconds. This is clearly not a landscape built for feet.

Except, scratch that. You look around and there are people everywhere. Some, like you, are walking down the asphalt. Many more have taken to the grass, occasionally forming sociable huddles around a guitar, or the Berlin equivalent of a picnic basket. It’s four years after Tempelhof closed for the last time and after the last aircraft departed – an Antonov AN-2 delayed by bad weather. Now this is a place being reworked for a different scale of existence. Before, everything needed to be colossal. This place is still vast – 100 acres larger than Manhattan’s Central Park – and in satellite photos it looks like a 400-hectare divot has been whacked out of Berlin by some continent-sized golf club. On the ground, it’s so big that there’s little sense of being in a city park at all. You’re not in Berlin anymore – you’re in Tempelhof.

You’ve been told that the terminal building, once one of the 20 largest buildings in the world, is well worth seeing. From this end of 27R it’s unimposing, a low dark silhouette perhaps a quarter-hour’s stroll away. Half an hour later you still haven’t reached it, and it has eaten the horizon. This 4,000-foot-long semicircle of hallways and hangers was designed to be the ultimate symbol of National Socialism – an eagle, stooping for a kill. Its roof was a mile long. Today the terminal building is a mass of private offices and rental space, and it’s frequently used for events that require a stage of epic proportions.

%Gallery-184233%Someone once said that Tempelhof airport united “the characteristics of an inland sea with the yearning for faraway places.” The only thing you’re yearning for right now is a cold beer, but the contents of your water bottle will have to do. You sit on the runway’s grass verge and watch everyone else. Most of them are clearly smarter than you, because they brought wheels: rollerblades, bicycles, skateboards and Segways. The runways funnel the speedy, and everyone else is meandering, enjoying a succession of moments. Nobody is hurrying because there’s no point – everywhere here is too far away to arrive quickly. You start to realize what you’ve been missing. It’s not just about geography – it’s also about time.

In a city famous for never standing still, this park (its official name: Tempelhof Freedom) is evolving into something much busier. Great strips of it are being put aside for formal development, while others are being used in more organic ways, the most charming being the allotment shantytown of Stadtteilgarten Schillerkiez. Here, wooden benches, pallets, boxes and barrels have been bolted together to form something excitingly ramshackle – a dab of Harry Potter, a sprinkle of Deadwood – and every hollow is filled with soil and sprouting plants (digging is forbidden, so this is the only way crops can be grown). Nearby, poles hoist animal sculptures into the air at the edge of grassland where dogs must be kept on a leash because the wildlife, including several red-listed species, is making a comeback. It looks like anyone could turn up and make something – a community art-space that would never run out of room. However, it might run out of time.

In four years, this park will be transformed for Germany’s International Horticultural Fair, creating an entirely new landscape specifically designed for foot traffic. Developers Gross Max and Sutherland Hussey will be improving access and installing pathways galore, although their redesign proposal affirmed a commitment to retaining “a contemporary prairie for the urban cowboy.” The same plan called for a 200-foot-high hill capped with an angel – not the first time a local architect has suggest Tempelhof has its own mountain. Other developments will include the relocation of the Central and Regional Library for Berlin to the park’s southwest edge – a wise move judging from the amount of people currently sat enjoying the afternoon sunlight with a book in their hands. The park will fill up, inside and out, and as the official redevelopment website notes, “the open spaces of Tempelhof Freiheit will not remain the way they appear today.”

You walk until your feet hurt, and you still get nowhere. So you turn around, and make your way back to the shallows, up the slope to the park gates at Oderstrasse (opened at 6 a.m.; closed at sunset). This late in the day everyone is reluctantly heading back towards reality, lingering on the grass to watch the sun redden and slip behind the apartment blocks in the far distance, at the other side of the world. Everything is in the pastel evening shades of England’s Dartmoor or the hills of Yorkshire. A wild place, uncolonized but belonging to anyone who wants it. How will it look the next time you visit? You’re glad you saw it now, before it all changed once again. And now you need that beer.

As the bus begins to pull away from the bus stop in Chania, I catch the old man’s eye again, giving him a thumbs-up through the window. He stares back blankly – then leaps to his feet, waving his arms, pointing, shouting. I raise my hands in an uncomprehending shrug, keeping the palms turned inward to avoid flipping him a mountza, the traditional Greek insult. He shouts louder, as if volume alone could break through the language barrier that had us miming to each other a few minutes ago. Then his body slumps into a pose recognizable the world over – “Oh, you bloody fool” – and that’s when it hits me in the stomach.

I’m on the wrong bus.

I have an hour before my ferry leaves the port of Souda, taking me away from Crete and back to mainland Greece. If I don’t hit that ferry, my carefully engineered schedule slithers through my fingers and I’m left untethered, without local knowledge, a decent enough grasp of spoken Greek or the money for new tickets. Without that ferry, I’m lost.

I sit down, by order of my knees, and stare out at the dusty, baked scenery as we rattle God-knows-where-wards. And then something strange happens. Panic ebbs away. I start to appreciate how lovely the light is, the rose-fingered sunset fading through the spectrum into that special glowing blue that enlivens domed roofs and door-frames right across Greece. I’m warm, I’m well fed, and I have no idea what is going to happen next – and it’s this last feeling that is so intoxicating right now.

Perhaps this is the wrong question. Perhaps it’s really this: why do I want travel to be easy?

When most people travel, they seek the unknown – either in a familiar, packaged, piecemeal form with the help of guides and tour operators, or the raw, improvised version that’s so popular with people young enough for their nervous systems to take it. I go off the beaten track using a third approach, which I like to call “Oh You Bloody Fool.” Somewhat appropriately, it’s a way of travel I accidentally fell into. I go places, things go wrong, and I fall through space, screaming. This is usually, but not always, a metaphor.

There’s a perverse joy in having your travel plans collapse around you. I’ve missed many flights and will doubtless miss many more. Once I get over the initial shock, once I’ve leaned against the nearest wall and cursed everyone up to and including the Wright Brothers, a calmness steals over me. I change. Lacking any alternative, I’m forced to become the person who can deal with this mess. My senses fly open, taking great gulps of the world around me, collecting data for my suddenly hyperactive brain to sift through in search of Life Or Death Answers. My heart thumps. My jaw sets. No time to waste – and off I go.

In “A Field Guide To Getting Lost” (2006), Rebecca Solnit says:

“The thing the nature of which is totally unknown to you is usually what you need to find, and finding it is a matter of getting lost.”

I’ve spent a lot of the last decade getting lost. I’ve been lost on England’s North York Moors in the middle of a rainstorm with the light fading – one of the few times I’ve genuinely hated not knowing my location. I’ve blundered across Berlin at 4 a.m. in search of my hotel, clutching a rain-dissolved paper map. I’ve suffered a thousand deaths of embarrassment in front of strangers, and I’ve eyed other travelers – so competent, so self-assured – with a mixture of envy and hatred. Why can’t I land on my feet instead of my face? Why does it all have to be so hard?

Perhaps this is the wrong question. Perhaps it’s really this: why do I want travel to be easy? When it’s easy, it’s a non-experience that our memories can’t get a grip on. Thanks to the miracle of GPS, we need never be lost. We can get from A to B knowing exactly what B looks like and having a machine dictate the entire route to us. Our technological support networks are vast and all-powerful, and our guides, physical and virtual, know more about the places we’re going than we ever will. We are mired in certainty and we need never put a foot wrong. But what if that’s not what we need – or why we travel at all?

I’m not pondering any of this as my bus takes me away from Chania. I’m fully in the moment, hunting for clues to where this bus is going, scanning the horizon for landmarks that tally with the map in my “Rough Guide.” There are 11 people on that bus. One lady is wearing a brown hat; one man has spectacularly hairy ears. These details are unforgettably burned into me by an elevated level of awareness …

I’m having the kind of travel experience I left home in search of.

Ten minutes later, the port of Souda hovers into view, and I realize, with curious disappointment, that I’m saved. I’m on the right bus after all. I unwittingly compensate by getting off the bus far too early, forcing me to sprint the final mile with a fully-laden backpack, and then I spend the first hour of my ferry ride lying semi-naked on the cool metal floor of my cabin, trying to bring my temperature down. The rest of the journey is a self-recriminating haze.

These days, being lost is at the heart of the kind of travel I love, filled with stories I don’t know in advance, positioned along the uncomfortable line between serendipity and disaster. Occasionally wild uncertainty is thrust upon me, as when I was robbed of my passport in Düsseldorf, seven hours before my flight home to England. (Ever wondered how long a UK emergency passport takes to put together? About six hours.) I’ve learned to appreciate these experiences for what they are – a living hell at the time, a treasure-trove of travel memories afterwards. All that said, I give myself lots of leeway nowadays, spacing out connections and over-budgeting where I can. I may be a bloody fool, but I’m not stupid.